The now-former deputy has been charged with first-degree murder, aggravated battery with a firearm and official misconduct in Massey's death after she called 911 to report a prowler. He has pleaded not guilty to the charges and remains in custody.
A review by Illinois State Police found Grayson was not justified in his use of deadly force. He was fired from his position with the Sangamon County Sheriff's Office on July 17, the same day the charges were filed against him.
Grayson's defense team requested his pretrial release from jail twice. In their latest request, the team argues in a motion filed earlier this month that he is currently under cancer treatment and will not receive adequate care in the Menyard County Jail, where Grayson is currently being held. They also stated that he does not pose a threat to Massey's family.
Judge Ryan Cadagin denied the requests on July 18 and Aug. 9, according to the circuit court.
Grayson's attorneys have not immediately responded to ABC News' question on whether they have already filed their appeal with the state Supreme Court or the date of the hearing. The Illinois Supreme Court has not immediately responded to ABC News' request on whether they have received the appeal.
In Monday's hearing, the defense requested more time for discovery -- the exchange of information between the prosecution and defense about witnesses and evidence they'll present at trial, according to the court. Cadagin granted their request and ordered a status hearing for Oct. 21.
Grayson's job with Sangamon County was one of six different police jobs he held over the past four years.
Prior to his employment with Sangamon, Grayson worked at the Logan County Sheriff's Office for just under a year. According to audio files obtained by ABC News, Grayson's then-boss, Logan County Chief Deputy Nathan Miller, expressed concerns over Grayson violating department policy and submitting inaccurate reports while discussing his mishandling of a traffic case.
Sangamon County Sheriff Jack Campbell, who announced he will retire at the end of August in connection to hiring Grayson, previously told ABC News that Sangamon County was not aware of this incident when Grayson was hired. Without knowledge of his disciplinary issues at Logan County, Campbell said that Grayson presented no red flags.
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"Some individuals would rather see our community divided and in turmoil, than allow me to continue serving as Sheriff," he said. "The health of me and my family, the Sheriff's Office, and our community has to be my priority."
Prior to Grayson's time in public law enforcement, he was discharged from the U.S. Army for unspecified "misconduct (serious offense)," according to documents obtained by ABC News.
ABC News also learned that Grayson was charged with two DUI offenses in Macoupin County, Illinois, in August 2015 and July 2016, according to court documents.
Grayson, 30, and a second, unnamed deputy responded to Massey's 911 call on July 6 reporting a possible intruder at her Springfield home.
Body camera footage shows Massey, who was unarmed, telling the two responding deputies, "Please, don't hurt me," once she answered their knocks on her door. Grayson responded, "I don't want to hurt you, you called us."
Later in the video, while inside Massey's home as she searches for her ID, Grayson points to a pot of boiling water on her stove and says, "We don't need a fire while we're in here."
Massey then pours the water into the sink and tells the deputy, "I rebuke you in the name of Jesus."
Grayson then shouts at Massey and threatens to shoot her, the video shows, and Massey apologizes and ducks down behind a counter, covering her face with what appears to be a red oven mitt. She briefly rises, at which time Grayson shoots her three times in the face, the footage shows.
Grayson said he feared for his life during his encounter with Massey, according to documents released by the Sangamon County Sheriff's Office in August.
"While on scene, I was in fear Dep. (redacted) and I were going to receive great bodily harm or death. Due to being in fear of our safety and life, I fired my duty weapon," Grayson wrote in his field case report.
The Menard County Sheriff's Office said in a statement that Grayson "is not receiving any preferential treatment, nor being afforded any privileges or benefits not afforded to other inmates of the Menard County Jail."
ABC News' Meredith Deliso contributed to this report.